Total Synthesis of (±)-Cephanolides B and C via a Palladium-Catalyzed Cascade Cyclization and Late-stage sp3 C–H Bond Oxidation,Journal of the American Chemical Society

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Total Synthesis of (±)-Cephanolides B and C via a Palladium-Catalyzed Cascade Cyclization and Late-stage sp3 C–H Bond Oxidation
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-04-09 , DOI: 10.1021/jacs.8b03015
Lun Xu ₁ , Chao Wang ₁ , Ziwei Gao ₁ , Yu-Ming Zhao ₁

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Herein, we report the first total syntheses of complex cephalotaxus diterpenoids cephanolide B and C from commercially available 5-bromo-2-methylanisole. Key to the success of this synthetic route is a palladium-catalyzed cascade cyclization reaction, which allowed us to efficiently forge the 6-5-6 cis-fused tricyclic ring systems found in the entire family of cephalotaxus diterpenoids. Additionally, site-selective late-stage sp3 C-H bond oxidation served as a key strategic element in the chemical synthesis of cephanolide C.

中文翻译：

(±)-头孢内酯 B 和 C 通过钯催化的级联环化和后期 sp3 C-H 键氧化的全合成

在此，我们报告了从市售的 5-溴-2-甲基苯甲醚中首次全合成复杂头杉二萜类头孢内酯 B 和 C。该合成路线成功的关键是钯催化的级联环化反应，这使我们能够有效地构建在整个头杉二萜类化合物中发现的 6-5-6 顺式稠合三环系统。此外，位点选择性后期 sp3 CH 键氧化是头孢内酯 C 化学合成中的关键战略要素。

更新日期：2018-04-09

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